Jeb Bush, right, and Donald Trump at the Republican presidential debate hosted by Fox News in Cleveland, Aug. 6, 2015. After failing to directly confront Trump in the first debate, Bush and his aides are under pressure to create a memorable showdown Wednesday to match a newly aggressive tone on the campaign trail.
DOUG MILLS
The New York Times

Jeb Bush, right, and Donald Trump at the Republican presidential debate hosted by Fox News in Cleveland, Aug. 6, 2015. After failing to directly confront Trump in the first debate, Bush and his aides are under pressure to create a memorable showdown Wednesday to match a newly aggressive tone on the campaign trail.
DOUG MILLS
The New York Times

Jeb Bush’s cerebral debate style faces a test: Donald Trump

On the debate stage, Jeb Bush has committed the sin of overexplanation, answering a pithy 1994 attack on his business career with so many details about leases and debts that a baffled crowd erupted into boos.

He has delivered high-minded put-downs, promising in a 1998 faceoff to establish a charter school “for people that distort the facts” and mischievously guaranteeing admission to his opponent.

And he has mangled seemingly simple sentences, vowing in a 2002 confrontation that “we can make Florida a bright – have a brighter future for – for all Floridians.”

In a Republican presidential debate season dominated by glib showmanship and volcanic personality, Bush, the former governor of Florida, faces a daunting challenge: How can he excite primary voters during Wednesday’s televised rumpus with a sober and cerebral style that can appear tepid next to the insult-spraying, nuance-avoidant, made-for-TV manner of Donald Trump?

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Now, after failing to directly confront Trump, the current front-runner, during the first debate, Bush and his aides are under pressure to create a memorable showdown with the real estate developer to match a newly aggressive tone on the campaign trail.

Since the first debate, Bush has mocked Trump’s immigration plan as “unrealistic,” released a biting online ad that captures Trump praising Hillary Rodham Clinton and accused Trump of trying to “insult his way to the presidency.”

In rigorous practice sessions that have crisscrossed the country in the past few weeks, Bush has been preparing pointed responses to Trump’s most frequent insults (he has called Bush “low energy” and a slave to donors) and crafting lines of attack on Trump’s history of liberal statements and unconventional policy plans, according to those who have been told of the plans.

“He has to challenge Trump now,” said Mac Stipanovich, an adviser to Bush during his 1994 campaign for governor who helped prepare him for debates that year. “He has to stand toe to toe with him and call him out.”

The difficulty for Bush, who has portrayed himself as the most mature and civil figure in the Republican presidential field, is how to inflict damage on Trump in front of a live national audience without diminishing himself in the process – a tricky task given Trump’s lust for the fierce counterpunch and Bush’s disdain for memorizing sound bites.

“Jeb is a nice man. He likes people. He wants people to like him,” said Newt Gingrich, the former House speaker who dominated several Republican debates during the 2012 presidential campaign. “He is up against a barroom brawler. And I think against barroom brawlers, if you are a nice man, you are better off keeping your distance.”

Interviews with current and former advisers to Bush and reviews of video footage from his debates as a candidate for governor reveal him to be a debater with as many deficits as strengths. On stage, his mastery of policy is almost unrivaled, but he struggles to synthesize it in compelling ways. He is capable of telegraphing deep compassion in one moment, but can convey unmistakable peevishness in the next. He defaults to analytical earnestness, rarely offering flashes of humor.

For better or worse, advisers acknowledge, his brand is self-seriousness.

Theatrics have failed Bush at times. During a dramatic 1994 exchange in Tampa, he dared the sitting governor of Florida, Lawton Chiles, to look into the eyes of Bush’s business partner, who sat a few feet away in the audience, and repeat an attack on the two men’s ethics.

“I know you don’t respect me, but I know you respect Armando Codina,” Bush said. “Can you look him in the eye and say that we’ve done anything wrong?”

Chiles, deploying his Southern drawl and a gift for outmaneuvering opponents, looked toward Codina, smiled and reflected on the businessman’s wisdom in hiring the son of a U.S. president.

“I think,” Chiles declared, “he made a good business decision when he took you on as a partner.”

The audiences broke into loud laughter. A few days later, Bush lost the election.

Bush has participated in about a dozen official debates since first running for public office that year. The majority of those encounters have been one-on-one with Democratic rivals, lacking the unpredictability of a crowded stage, like Wednesday night’s forum. After losing the 1994 election to Chiles, he prevailed in the 1998 governor’s race against Buddy MacKay, Chiles’s lieutenant governor, and in his 2002 re-election race against Bill McBride, a lawyer.

In many ways, Bush’s general election debates against MacKay are a model for how he might treat Trump in the long term. MacKay set aside his usual regal bearing and relentlessly attacked Bush as an inexperienced, untrustworthy child of privilege. Bush’s strategy was simple: deftly defend himself, sow doubts about his rival, but avoid excessive confrontation to magnify MacKay’s smoldering temper.

In a 1998 debate, when he was asked about his business dealing with a Nigerian corporation, Bush pivoted to discuss a controversial investment that had earned MacKay $500,000. But instead of mocking it, he suggested, generously, that there was nothing scandalous about the profit.

“I’m happy that the MacKay family made half a million bucks on a good investment,” Bush said, “I don’t see anything wrong with that. I applaud you for doing that.”

MacKay looked slightly dazed.

Seventeen years later, MacKay said he had miscalculated. “I expected him to be more negative than he was,” he said in an interview last week. “I may have been too negative myself, as a matter of fact.”

In the same debate, Bush showed unexpected humility when asked about his relationship with Florida’s black voters, who had flocked to his opponent four years earlier. “Republicans have ignored the black vote in this state, and I was part of that, and it was a mistake,” Bush said.

His tendency to cram as much information as possible into an answer has diminished since 1994, when he became entangled in a long-winded explanation of a real estate transaction, describing a maze of leases “we had to assume,” a debt “borrowed by an investor in the deal” and “specific obligations.”

But the habit resurfaces now and then.

“His mind rebels against the oversimplification that passes for succinctness in the television debate,” said Stipanovich, the 1994 adviser. “Instinctively he finds it incomplete and unsatisfying. So he overanswers.”

As Bush prepares for a televised brawl with Trump, that 1994 debate against the wily Chiles looms larger than ever, a searing lesson about the dangers of taking on an unpredictable opponent.

Midway through that face-off, which seemed like an agonizing draw, Bush, the newcomer, suggested that Chiles, the two-term governor, had lied to “strike fear in the hearts of the voters.”

Chiles stood silently, resting an elbow on the podium and taking it all in. Then, peering over at Bush and jabbing his finger, Chiles delivered an unscripted line about himself that changed the course of the campaign.

“I want to call attention to this old, liberal liar,” Chiles said self-mockingly, pausing for effect. “The old he-coon walks just before the light of day.”

The camera captured a seemingly baffled Bush looking around the room and then toward the moderator, NBC’s Tim Russert. Neither candidate’s aides had any idea what Chiles meant. But across the state, an entire generation of native Floridians understood.

The he-coon is the oldest and wisest member of a raccoon pack, a cunning hunter who knows exactly when to strike. Chiles used the old Southernism to make it clear: He was not done being governor yet.